ArticlePrecision chemistry2026
Iridium-Catalyzed Regio- and Enantioselective Hydrogenation of 5‑Alkylidene Cyclopentenones.
Article in Precision chemistry, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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1 citing paper in PubMed.
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Authors and funding
5 authors.
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Abstract
The regio- and enantioselective hydrogenation of the CC bond in molecules with two or more CC bonds of the same type is very challenging but highly desirable. Herein, we report a regio- and enantioselective hydrogenation of 5-alkylidene cyclopentenones catalyzed by an Ir/BiphPHOX complex, delivering the corresponding mono- and double-hydrogenated products in excellent results, respectively (5-substituted cyclopentenones: up to 99% yield and 98% ee; 2,4-disubstituted cyclopentanones: up to 99% yield, 16:1 dr, and 99% ee). For the chiral 2,4-disubstituted cyclopentanones, the results of mechanistic studies indicated that both the exo- and endocyclic CC bonds of the substrate can be preferentially reduced with the exocyclic CC bond undergoing hydrogenation more readily. The ester group in the substrate plays an important role in improving the reactivity and controlling the stereoselectivity of the product. The reaction was successfully conducted on a gram-scale, and the hydrogenated product can be readily derivatized.
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